


Self Insert

by mattzerella_sticks



Series: Season 15 Inspired [8]
Category: Supernatural
Genre: Age Difference, Bad Ending, Betrayal, Bisexual Chuck Shurley, Chuck Shurley Has a Crush on Dean Winchester, Chuck Shurley is the Big Bad, Coda, Episode: s15e05 Proverbs 17:3, Free Will, Headaches & Migraines, Implied Sexual Content, Love Potion/Spell, M/M, Meta, Metafiction, Mind Manipulation, Overdosing, Post-Episode: s15e06 Golden Time, Sam Winchester's Visions, Scheming, Season/Series 15 Spoilers, Temporary Character Death, Writer Chuck Shurley, Writer's Block
Language: English
Status: Completed
Published: 2019-11-24
Updated: 2019-11-24
Packaged: 2021-02-26 18:21:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,860
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21542962
Author URL: https://archiveofourown.org/users/mattzerella_sticks/pseuds/mattzerella_sticks
Summary: Ever since finding out that Chuck has been writing their lives, the Winchesters are going off script more than usual. And each act of free will spits on all of Chuck's work and muddles his sharp, writer's mind. It's bad enough he has to babysit a powerful demon he brought back from the Empty, but now he can't write the ending the Winchesters deserve. How can he create an epic, gut-wrenching ending when he's being given domesticity, wallowing, and a badass Castiel to work with. All of it useless to him.There's nothing anchoring his work. No puppeteer to pull the strings. But somehow Lilith proves her worth and finds the silver lining in the stormy skies.
Relationships: Castiel/Dean Winchester, Chuck Shurley & Lilith, Chuck Shurley/Dean Winchester
Series: Season 15 Inspired [8]
Series URL: https://archiveofourown.org/series/1517543
Comments: 3
Kudos: 62





	Self Insert

**Author's Note:**

> So I loved "Golden Time". Meredith Glynne is the gift that keeps giving. I have a lot of ideas on different codas to write, and I originally had a different idea in mind to start. But then this came together and there was this one piece of dialogue that I wrote that NEEDED to be seen.
> 
> Lilith is a great character and I am glad Chuck brought her back. I had a lot of fun writing her. Just like I enjoyed a lot of the meta stuff that I included in this piece.
> 
> This season rocks :D Enjoy!

Chuck raids Becky’s bathroom cabinet, mirrored door swinging wildly on its hinges while he searches for aspirin. Another migraine rips across his temple, flaring as powerful as a dying star. He curses, tossing lotions and bottles randomly until he finds the economy sized tub. “Thank me,” he sighs, grabbing it and twisting the cap off. One pill wouldn’t cut it, so Chuck poured the bottle down his throat until his cheeks puffed. Then he races to the kitchen for a pitcher of water to wash it down with.

Lilith watches on, unamused by the laughable scene of God overpowered by a simple headache. “Really?” she starts, waiting until Chuck leans against the counter with an empty pitcher in hand, “You couldn’t snap your fingers and make it go away?”

He shoots her a glare but she doesn’t wilt. “It doesn’t work like that.”

“But swallowing enough pills that could take down all of Jonestown helps?”

“Maybe?” Chuck shrugs, “Power of suggestion?” As he says that, another beat of pain flares up. Dropping the pitcher, he rubs at his forehead. It shatters against the tiles. Chuck walks away, muttering, “Clean that up.”

“Oh, that’s all I am now?” Lilith snarls, defiant, “Your _maid_? Not even good enough to be a plot device anymore?”

Another headache wiggles at the base of his skull, where a set of fiery white eyes burn into him. “You weren’t even that good of one to begin with.”

“Excuse me!”

Chuck scrubs his hands over his face, frozen, waiting for the avalanche he knocked over to bury him. Lilith stomps towards him, each blow to the floor adding to his already drumming head. She claws at his arm and forces him to look at her. “ _What_?”

“You know what,” she says, squinting up at him, “You wake me up, bring me here, give me one night of freedom and then…? _Nothing_ ! There’s only so much you can do in a damn house. Especially one that doesn’t have any _cable_!”

Chuck copies her disdainful expression. “There’s wi-fi.”

“That doesn’t help me when _you_ have the only laptop!” Lilith yells at him, “Give me something to _do,_ dammit. Otherwise just send me back to the Empty!”

“I gave you something to do,” he lobs back at her, “And you did it _poorly_.”

“I got you the Equalizer!”

“You got _rid of_ the Equalizer!”

“Which I _still_ haven’t been thanked for,” she says, hands flying above her, “I know you’re the Almighty Father but would it kill you to express the smallest amount of gratitude? I mean, no wonder Lucifer fell like he did…”

Chuck feels anger bubbling up inside him. Instead of wrecking his current base of operations he directs the maelstrom towards a distant galaxy light years away. Decimates three planets and freezes the core of their sun so the rest of that solar system dies slowly. “I wanted it.”

“For what reason?” she asks,”What reason would _possibly_ warrant you keeping a weapon that can _kill you_ around? It makes no sense.”

“It doesn’t have to make sense!” Chuck tells her, voice loud and enriched with power, “Out of the two of us here there’s only one God and it’s me… I don’t have to tell you _anything_ . I don’t have to _keep you here_.”

“But you do,” Lilith says, “Not out torturing the Winchesters or their friends. Not back in the Empty sleeping for the rest of eternity. No, I’m here because you _need_ me. Need me to sit around and read through every different ending you’ve written, being slowly driven mad because I’m the one forced to _entertain_ your _mediocre bullshit_ \- nggh!”

Lilith hovers inches off the ground. She claws at her neck, where an invisible force applies excess amounts of pressure. Breathing doesn’t matter, but with her windpipe crushed she can’t speak. The pain comes when Chuck’s eyes glow a blinding blue and parts of her essence shrivel from the exposure.

In a blink the light show ends and she falls. Chuck steps to her, glaring at her crumpled form. “You want to know the real reason why you’re not back in the game?” he scoffs, “The Equalizer was only number one on the list of things you _seriously_ screwed up. Because of you, the Winchesters know I’m working behind the scenes! You took my hand and laid every card I had on the table. Your whole chapter went _nothing_ like I _wrote_!”

“That wasn’t my fault,” she coughs, wiping at her mouth, “You stuck me with _lumps_ and expected _statues_. Of course nothing was going to plan.”

“Maybe if you tried harder the Winchesters would have responded better -”

“Winchesters?” Lilith laughs, a rough, hollow melody that grates on his nerves. “Kind of a roundabout way of saying _Dean_ , don’t you think?”

Like being shot by Sam again, Chuck recoils from the strike. He considers flexing his power, destroying her and bringing her back again, only to settle after deeming it a waste. “No, it’s not… you failed with both of them -”

“So I was supposed to seduce _both_ of them?” Lilith says, “Because I read your flimsy excuse of a first draft and that part with Sam wasn’t included. In fact, Sam was hardly mentioned in it at all. You still nursing a… _wound_?”

Chuck brushes the joke off, shoulder tensing under his jacket. Tendrils of pain squeezing the muscles where the bullet rests. “Sam wasn’t that important then… it was you and Dean -”

“And the knock-off erotica you wrote in which I, trapped playing a barely legal philosophy major, seduce Big Brother Winchester and we have crazy sex where I’m moaning and screaming ‘That’s it! Slam into my tight, little, virginal ass, Dean’!” She writhes on the floor, giving a Meg Ryan-worthy performance. Lilith stops with one hand tangled in her hair while the other supports her arched back. Bedroom eyes replaced with a harsh gaze. “Sorry I didn’t become the little porn star you wanted _daddy._ ”

He grabs her arm and drags Lilith to her feet. “I didn’t realize you treated that scene like a joke.”

“I could have,” she tells him, “Really play up the innocent school girl routine, but whatever I would’ve sold Dean wouldn’t have bought.”

“Of course he would have,” Chuck says, defensive, “This is _Dean_ we’re talking about. He should’ve been all over you in that motel room.”

“Well he wasn’t.”

“Because you weren’t playing up your character’s sexuality enough,” he argues, “I made it really easy for you, too, what with all the aphrodisiacs I wrote in. Do you know how hard it is to insert ideas into someone’s head that they should change the layout of their motel rooms so they had mood lighting and antlers everywhere? In such a short time? No!” His finger jabs at her, close enough he nearly pokes her eye. “Since I’m ninety-nine-point-nine-nine _infallible_ than the problem was definitely _you_.”

Lilith scowls at him, sharp teeth poking between her lips. “Like I keep telling you, it wasn’t me - and it also wasn’t _you_. It was Dean, he _wasn’t interested_.”

“Because you weren’t -”

“No!” she shouts over him, “Because he’s not the Dean you knew! Because he realized how creepy it is hooking up with a girl who’s almost _half his age_ ! Who only seconds before was crying about how awful her life was because she felt like she had no purpose. I bet that at no moment of knowing ‘Ashley’ did he think her purpose was to happily take his wrinkled dick and fondle some saggy balls for fifteen seconds until he came and fell asleep without even attempting to return the favor! I’m tired of saying this but he is _not_ the man you know anymore!” Lilith’s chest heaves with the force of her words, a few of the figurines in the room tipping over from how wild her power shot during her tirade. Like whips of electric energy she tore through the room, shattering picture frames and upending Becky’s model Roadhouse.

Chuck watches her through slitted eyes. He snaps his fingers and the room repairs itself. “You don’t know what you’re talking about,” Chuck says, “Of course I know him - I know _all_ of them. They’re _my_ creations. Nothing’s changed about them, not at all.”

“So you’re completely ignoring what showed up today?”

A shadow passes over his face at the question. Another tidal wave of pain roars through his mind, every nerve in his body swept in its destructive path. “It’s nothing.”

“Sure it isn’t,” Lilith says, backing away, “That’s why you spent all that time ripping it to shreds only for it to reappear on your desk like it never happened -”

“Lilith.”

“I took a peek, of course,” she admits, “I found it… I didn’t immediately hand it over. Like I said, I’m _bored_. It was interesting… very different than a lot of other things I’d been forced to read.”

“Stop it, I mean it -”

“Dean Winchester, our charming man of action, holed up in his room eating his feelings and nursing some heartbreak,” Lilith mocks, tone heavy with cruel delight. “Sam, the boy afraid of his own powers, taking ownership of his affluence and ability with magic. And Castiel the - actually, I don’t really know how to describe him. The angel never really comes up in your writings. I don’t know why seeing how _hot_ that action scene was. If you wanted me to seduce him, I wouldn’t really mind… if Meg could do it then so can I -”

“ _Enough_.” Chuck snarls, windows shattering all around the house. Pain from the migraine becomes too much to deal with so he sinks to his knees, unable to use his powers and fix the broken glass. All he can do is focus all his energy on his breathing while he fights the chaos of free will tearing up his future.

When he feels more in control again Chuck opens his eyes and chances a look at Lilith. The angry expression on her face melted into a more unusual one. Curiosity easily shines in her eyes at his pathetic display, outlined with an odd hue of fear. Returning to full height, both school their expressions into masked indifference.

“Those pages were _garbage_ ,” he tells Lilith, “they were… _fanfiction_ . It’s not how it’s _supposed_ to go. Sam’s happiness… Castiel’s confidence and Dean…” Chuck can’t bear to utter the next few words. “Whoever wrote those doesn’t know all the work I put into creating these characters. All the specifics of their characteristics that makes them who they are. That makes them butt heads and become their own worst enemies! I’m the author! Whatever _I_ write is canon! And I do _not_ like being _mocked_.”

“But you were, Chuck,” Lilith says, a softer approach, “Today _you_ wrote the fanfiction… the story where Dean leaves Sam behind to drown in booze and women didn’t happen. Sam choosing to sacrifice the body of the woman he loves to destroy Rowena’s magic didn’t happen. Castiel being too late to save that mother and kid because he was paralyzed by his depression… _that didn’t happen_ . None of what you’re writing will happen if you sit behind a desk and _pray_ for it to work. Sometimes you need to put the effort in and bend the rules to fit your game.”

Chuck arches a brow in her direction. “Deus ex machina?” he frowns, “I kinda prefer keeping my arrival until the very end… I am _God_ after all. If I show up too early then where’s the plot gonna go?”

“And yet the story of the Winchesters keeps going even though you're a recurring character,” she shakes her head. Lilith inches closer to him, smirking. “This isn’t the time to be holding back. Grand finales mean bringing in your heavy hitters, like _yours truly_ . Who cares if _you_ show up early? Every moment from beginning to end should be filled with adrenaline and action and not this… domestic crap.”

It’s a convincing argument, Lilith presenting her case with honeyed words fashioned to sweeten his ears. Except he doesn’t trust her enough to suspect that her goals are far less charitable than helping him with his runaway characters. In a room full of quickly-closing corners, however, he will take the first exit presented.

“That’s not a terrible idea,” he says, walking towards the study. Lilith follows. “Since Belphegor’s arc wrapped up way too early for _him_ to be the Big Bad… there has been something missing in my work. No wonder Dean and Sam have been circling the drain!”

“It helps they’re already gunning for you,” Lilith adds, sitting in a nearby chair, “Good luck taking _you_ off the board though seeing you’re _God_.”

Chuck relaxes behind his desk, staring at an open Word document. “But they’re putting up a united front. Kind of makes it hard to have one kill the other when there’s nothing driving them apart.”

“You could have Sam find out what Dean said to -”

“There’s _nothing_ driving them apart.”

“Then _be_ what drives them apart.”

“ _How_?”

“I thought you were the writer here?” she scoffs, swinging her legs up over the armrest.

He rolls his eyes. “You said you wanted something to do, right? Help me come up with a wedge.”

“Kind of a waste of my skills…”

“You’d rather I send you into some other girl,” Chuck asks, “have you try and seduce Dean all over again?”

Lilith scowls. “Why don’t _you_ try and seduce him.”

“What?”

“You seduce Dean,” she repeats, “You’re so obsessed with who he sleeps with, clearly you’re sporting a chub for the guy. Every scene you write with him in it makes it obvious, even the ones where he dies at Sam’s hands. No one needs to know how handsome a guy is moments away from death.”

Chuck shrugs, nervously fiddling with his glasses. “Debatable…”

“So why don’t you hop on his dick and get off mine.” She reaches behind her for one of the figures on display, snatching a Dean with opposable joints. Swinging his arm, Lilith takes the knife in its hand and has the miniature Winchester stab himself over and over again.

He pays her no mind, mulling over Lilith’s sarcastic suggestion. “Y’know…” Chuck mumbles, putting on his glasses, “that could work…” Chuck’s fingers begin typing. The story unfolds easily now that the missing element - himself - was added to the page. A wicked smile unfurls the more he types.

Hours pass, and Chuck has a working idea of how the Winchesters’ world will end.

* * *

Sam carries a few books through the Bunker’s main room when he hears the door open from above. Glancing up he finds Dean casually strolling down the steps. A swagger in his posture that hadn’t been present in a long while. So taken aback he nearly let his brother walk away without the stern interrogation he planned.

“Dean,” he starts, “where were you?”

Dean pauses under the archway, facing away from Sam. His hand pressed against the wall. “Out.”

“Out?” Sam scoffs, “That’s it?”

“Yeah. I was out.”

“Without leaving a note or answering mine or Cas’s calls and texts?” Sam stomps over, scowling, “You complain all this time about him ignoring us. And the moment he gets here you turn tail and leave? What’s the matter with you?”

Dean shrugs, showing a sliver of his handsome profile to Sam. “Had better things to do then waste hours running in circles with you and a fallen angel.”

Sam’s expression hardens. “Out, huh?” he asks, “Did you go to the jerk store?”

“No,” Dean says, “now are we done? Can you go back to your bitch party?”

“Dammit, Dean!” He grabs his brother’s shoulder and spins him around, stomach clenching at the disinterested stare that greets him. “I thought we were done with this, man! If we’re gonna have any chance to take down Chuck than I need you here, with us. Knowing he’s still playing with our lives it’s… I know it’s hard. But none of us will make it out alive if we’re keeping each other at a distance.”

Dean pouts throughout Sam’s speech, but a spark flickers in his eyes. His tight shoulders droop under an invisible weight, and the indifferent mask breaks. “Sorry,” he says, “I… I know. I get it. But I didn’t want to sit and read and… I found this case in Texas. Thought Chuck was tied to it. Figured you and Cas were okay to sit tight and handle the research while I hit the field.”

Sam sighs, the knot in his chest unwinding. “That’s… okay. Wish you still told us but… did it pan out?”

“What do you think?” Dean shrugs. He scrubs a tired hand over his perfect jaw, plush lips stretching under his touch. “It… it didn’t turn out so well. Wasn’t so much Chuck as it was a djinn. Handled it anyway.”

“That’s… that’s good,” Sam says, attempting a smile, “You feel any better killing it?”

He shakes his head. “Not exactly what I wanted to kill at the time.”

Seeing his brother crack open his hard shell eases some of the tension between them. Sam inches closer, bringing his brother into a hug. Going slow to give Dean enough time to escape. When he doesn’t, Sam wraps his arms around his brother. “We’ll find a way to get Chuck,” Sam tells him, “and the second we get him you’ll have first dibs.”

Dean shifts in his hold. “Funny thing, Sam,” Dean mumbles, “I’m not in the mood to kill Chuck, either.”

“What -”?

_Snkkt_

A burning pain rips through his chest from where the blade sunk in. Blood rushes up his throat and bubbles in his mouth, Sam spluttering while it leaks from his parted lips. The books in his hand crash to the floor and he stumbles backwards in shock.

Dean watches him with a soft glee highlighting the crinkles near his gorgeous eyes. Sam darts his gaze from his brother’s face to the red-stained knife in his hands. His hands rush to cover the wound, but the blood continues gushing. “W-what…?”

“Enchanted,” Dean tells him, wiggling the weapon like a toy, “got it from a special friend.”

“You…” Sam’s legs give out and he crumbles to the floor, “How…”

A slow clap echoes in the room, drawing Sam’s attention. He uses all the strength left in him to crane his neck to where the sound originates.

Chuck, in a burgundy blazer and pressed black slacks, stands over them. Sam’s eyes widen as he descends the stairs. “Y-you,” Sam mutters, on his hands at this point, “How… why…”

“It’s easy,” Chuck says, passing him on his way to Dean. His brother welcomes him gladly, adoration shining. Darkness edges his vision, but Sam can still see how Dean nuzzles Chuck’s hand when it rubs his cheek. Accepts a kiss as he bleeds out in front of him. “Dean finally understands his place in the story…”

“Your word is law, baby,” Dean says, “Whatever you want, I’ll do.”

“You know what I’d really love…?”

In his final moments Sam becomes a third party to the scene about to play out. Chuck whispers to him, mouth hidden. Dean nods and drops to his knees. His last breath intermingles with the jingle of Dean removing Chuck’s belt. Chuck’s zipper being undone one of the last thing he hears. Sam’s life eeks out of him, and he dies knowing his brother has and will continue to service the very being that controlled their lives from the beginning.

“If only you knew, Sam,” Chuck says, “the glory that comes from giving your life to God…”

* * *

Chuck waits for Lilith to finish, leaning on his desk while she reads the printed pages. It’s been very silent, a worrisome song for writers when faced with readers. But given the variety of faces she shuffled through Chuck feels his nerves untangling.

“I have to say,” she says, “I’ve said this before and I didn’t really mean it all those other times. But when I say this is great… I actually mean it.”

“Really?”

“Well?” Lilith shrugs her shoulders, “it’s better than anything else you’ve done. It’s fresh, you’re not rehashing any of the old plot points that’ve come and gone. There’s a strong point of view here… Really appreciated you using Sam’s blood as lube -”

“I knew you would.”

“And that part where Cas walked in on you fingering Dean,” she continues, slapping the papers, “I cackled! Forcing him to stay until you finished and then making Dean kill him was brilliant.”

Chuck blushes under the praise, waving her off. “It just grew organically from where the story was going.”

“And then some…” Lilith lies his work flat on her lap and stares at him. “Now the only question I have is… will this ending actually _happen_?”

“Oh… I think we’re winding closer to the end than anyone realizes…” Chuck turns the laptop around and shows Lilith the news article he found celebrating a local celebrity named Leo Webb. “And to thank you for the inspiration… I have another job for you.”

Lilith sinks to her seat. “I’m interested.”

Chuck explains the scene he has waiting, the unfinished threads he will quilt together later on. The more he talks about it the better the finished product becomes in his mind. An excitement that hadn’t existed inside for a long time squeezes his heart. He looks forward to leaving Becky’s house and getting his hands dirty. A joy he thought only came from creating worlds resurfacing in the opening act of destroying one.

Writing about Dean and Sam for so long made him forget who the _real_ star of their story was. And it’s high time he reminds them.

* * *

Sam shuffles into the kitchen, rewinding through the horrible dream he experienced. One of the worst since he shot Chuck with the Equalizer. Thinking about it sends shivers racing up and down his spine like it’s NASCAR. The cars on the makeshift track speed faster when he finds Dean stuffing cereal into his face.

“Morning Sam,” he says, waving with his spoon, “Wanna pull up a seat?”

He doesn’t answer. Sam books it towards the coffee pot and debates pouring the drink over his eyes. Instead he grabs a mug from the cabinet above and fills it. Quickly, uncaring to how a few drops splash onto the counter. The faster he makes his coffee the sooner he can hide in his room until he wipes his memory of the horrible nightmare.

Dean won’t let him. When Sam turns to leave, he’s blocking his escape with a stern frown. “Sam?”

“...Yeah?”

“What’s wrong?”

Sam shuffles his feet, unable to meet Dean’s questioning stare. His brother asks again. “I can’t, Dean.”

“Why not?” he asks.

“Because if I say it, out loud it’s…” Sam sighs, “it’s real.”

Dean nods, leaning against the island. “Another vision?”

“Yeah…”

“How bad was it?”

“So bad.”

“And you’re _sure_ you don’t want to talk about it?” Dean asks, “Y’know… maybe if you let me know I can -”

“No.”

“No?”

Sam shakes his head. “No. Trust me Dean, this… you don’t want to know…”

**Author's Note:**

> So what did you think? I hope you had a blast reading this as I did writing it! From the cracky antics to the serious plot points... the shift was very satisfying!
> 
> Let me know what you thought! Drop a kudos & comment below.


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